Double Date
by linsteadloverr
Summary: Mostly a Will x Natalie fanfic (from Chicago Med, as if you didn't know) and a good amount of Linstead


**Author's Note: I'M BAAACK! Did you miss me? Wow it's been a while. Quick update on me what have I been doing lately? Becoming overly obsessed with Quantico and Chicago Med, YAY!**

 **I posted on tumblr a few days ago for someone to post a Will x Natalie fic with Linstead or something and then I thought screw it I want it and if I'm asking for it, why not write it because I'M SO OBSESSED I HATE IT. (What has my life come to lol.) So, here I am. Saying that I wouldn't have time to write this, but because I'm so obsessed, sleep has to wait and I needed to finish this, because again, I am obsessed.**

 **I hope you still want to read it after this obnoxiously long author's note, but hey I missed y'all. So, read on and enjoy!**

* * *

"Will. Come on, we gotta leave." As Jay tied his shoes he could hear the rustling coming from Will's bedroom. "You would think you would be faster knowing your girl hates when people are late."

Will emerged from the bedroom and continued to search for his keys, "Oh whatever, she'll be fine." He finally found his keys on the living room coffee table and grabbed them. He faced Jay, "Do I look okay? I mean, you know what, nevermind."

Jay chuckled, "Wow, dude. I've never seen you so nervous," Jay smirked after he heard a scoff come from Will's direction. "And yeah you look great. But it probably won't matter because Natalie will kill you when we show up 15 minutes late to pick her up."

"I'm not nervous." Jay looked at Will with raised eyebrows. "Okay fine. Maybe a little. But that's only because I don't know how this whole double date thing is going to go. I mean I know her and Erin are sort of friends, but still it's going to be awkward. We just started dating."

Jay responded, "Oh come on, you've been seeing each other longer than 'we just started dating'. But don't you worry, I won't share any of your embarrassing childhood stories." Jay looked up to Will glaring at him. "Maybe I will just to cut some tension. You've embarrassed me enough in front of Erin, it's your turn now bud." Jay laughed as he patted his brother's shoulder and walked out the door with Will following shortly behind.

The brisk, autumn Chicago air hit their faces as they walked to Will's car across the street from the apartment complex, "Do you know who's watching Aiden then since we're having a date night?" Jay asked and looked over at Will who tried to hide his smile by looking down.

"April, I think. Nat dropped him off earlier this afternoon. I think April's taking him overnight and we're picking him up in the morning."

"We, huh. Does that mean she's spending the night at your place?" Will just smiled back at him as they got into the car. "Well, I guess that means I can't crash at your place tonight then."

"Oh you know you would've ended up at Erin's anyway. So why haven't you two moved in together yet, again? I mean you signed over your lease to me now, so I'm assuming you were hoping…"

"Stop. Don't you dare bring that up at dinner, too. Erin doesn't know about that yet."

"Really? Well, let's just hope that Nat doesn't blow that one for you bro." Jay sighed.

* * *

The rest of the ride to Erin's place was completely silent except for the low buzz of the music. When they pulled up, Erin was outside tapping her foot impatiently and then breathed out a sigh of relief at the sight of Will's car pulling up. She smiled slightly as she approached the car.

As the car came to a stop, Jay stepped out of the car to greet his girlfriend, "Hey." He smiled and kissed her on the cheek and opened the backseat door for her. "After you." Erin blushed as Jay got in beside her. After they got all settled in, Will started driving to Natalie's apartment complex.

"So, Will. Are you ready for us to grill Natalie about your relationship?" Erin questioned and she noticed that Will glanced back at her through the mirror. "Or I guess we could just embarrass you the entire time. Either one works for me."

"Er, he wants to get laid tonight, so grilling them about their relationship, whatever it is, will only make sure that doesn't happen."

"Well, looks like we're going for the grilling then." Erin chuckled and patted Will on the shoulder.

"Yeah, yeah. I get it all of these threats, but just so you know I've prepared her for this situation since Jay insisted that we go on this stupid double date." Will huffed.

"Let's just hope she doesn't cut your balls off first for being so late."

"I texted her before we left my apartment that we would be a little late and she just said to go up to her apartment to pick her up. So I will do that quickly so we are not completely late for our dinner reservations." Will said matter-of-factly. "And here we are. So I'll be right back. No monkey business in my car please and thank you." He jumped out of the car and lightly jogged to the door of the building.

"Well, now that he's gone for a bit, we can do this." Jay said mischievously as he leaned into Erin and they began a heated make-out session.

Between kisses, Erin huffed out, "Jay, they're going to be back soon. We need to stop before the windows get too cloudy and then they'll know what we were doing."

"Like they would really notice." Erin smiled back at him and the makeout session continued.

* * *

Meanwhile, Will lightly knocked on Natalie's apartment door. He heard her scrambling behind the door and after a few seconds she finally opened it. "Hey." she said as she zipped up her tall brown boots.

"You know if you wear those, it's going to take a long time to get those off tonight." Will smirked.

"Oh, shut up."

"You look beautiful."

"Thank you." She leaned up and wrapped her arms around his neck and gave him a chaste kiss on the lips. She smiled into the kiss after she felt his arms tighten around her. She pulled away after a few seconds, "You don't look half bad yourself."

"So, are you all ready to go?"

"Yeah, I'm ready. I just need to grab my purse. The real question is if I want to go to this thing. What is your brother calling it again? A double date?" Will sighed, "I'm seriously going on a double date with my boyfriend's brother and his girlfriend who can be a little intense sometimes." Natalie ranted as she grabbed her purse off the side table and shut the door behind her.

"I know you don't want to, but apparently this is really important to Jay that we all get along, and they want to get to know you and I want them to know how amazing you are and how beautiful of a person you are."

Natalie blushed at him as she pushed the down button, "You can keep those compliments coming and I'll be on my best behavior for you tonight."

"Just for the dinner part though okay? Because then I'm kinda hoping you won't be on your best behavior when we go back to my place." They stepped into the elevator. "And you can be one of my favorite quality of yours. So damn sexy."

"Will Halstead, you are everything but subtle aren't you." Natalie laughed as she placed her hands on his chest.

"But seriously, thank you for coming tonight." He kissed her forehead and looked back down at her, "It means a lot to me that even though you don't really want to go, that you're coming tonight. And also for letting April take Aiden for the night too, so we can spend so more quality time." He smirked.

"Of course. And you know sometimes a mom needs a bit of time away from her kid so she doesn't go crazy."

"I don't want you to think that I don't love when Aiden is around though. Some of my favorite moments are simply just watching you be his mom." The elevator stopped and the doors opened and they walked into the lobby. Will slipped his hand into hers.

"I know. And I also know that I don't say this enough, but thank you for always being so great with him." She shivered as they walked outside towards his car.

"I love the kid. What can I say." Will almost stopped dead in his tracks as he saw what was happening in the backseat of his car. "They're making out aren't they." Natalie laughed and nodded as she glanced at the car. "I swear they act like horny teenagers and we're the mature adult relationship." As they got closer, Will tapped on the glass and laughed as Erin and Jay quickly jumped apart. He opened the door for Natalie and let her get settled in before he made his way to the driver's side.

"Hey Natalie. How are you?" Erin spat trying to catch her breath and fix her shirt from her heated make out with Jay.

"I'm really good thank you, and you guys?"

"We're good." Jay replied.

Will got into the car and turned it on, "Okay, are you all ready to get this night over with?"

"Will, come on, it's going to be fun. Stop being such a debby-downer." Jay said before glancing over to Erin who was staring out the window at the city and he did the same.

Will glanced over to Natalie and she gave him a small smile. He grabbed her hand over the console and rubbed his thumb along it. She looked down at her lap trying not to blush too hard. He sighed. He just wanted this night to be over so they could just be by themselves, even if it wasn't just to have sex. He loved their talks and she was a pretty damn good cuddler as much as hates to admit that he loves to cuddle.

* * *

"Well that was a pretty good meal, I will give you that." Will stated as he leaned back in his seat and put his arm over the backside of Natalie's chair. She nodded in agreement as she took a sip of her water.

"This is our favorite spot." Jay smiled at Erin. They were foodies at heart and since neither of them could really cook, they seemed to go to The Purple Pig quite a bit.

The entire dinner so far was only filled with idle chit chat that really didn't have to do with anything other than work.

"So, Natalie…" Erin started. Will sighed, he knew this was coming eventually. He moved his arm from the back of the chair and placed his hand on Natalie's thigh and gave it a little squeeze. "What really made you give this guy a shot at a relationship? I mean he doesn't have the best track record." Will scoffed.

Before Natalie could answer, Jay interrupted, "Yeah, it's not like he's the best choice of a guy at the hospital. I hear Rhodes is pretty far up the list for most of the women there." Natalie made a face of disgust at the mention of the possibility of a relationship with Connor (sorry Connor x Natalie shippers, I'm petty).

"Umm, well." She didn't really know how deep she wanted to get with these people, but they just wanted to make sure her intentions were good, right? She glanced at Will and he was staring intently at her waiting for her to respond, "I guess you could say we were two peas in a pod when I was pregnant with Aiden and before that. I got his jokes, was one of the only ones able to deal with his crap and he would listen to me rant. Then when I was in labor during that horrid snowstorm so my family couldn't make it on time," Will chuckled in memory of that day, "he held my hand through the worst pain in my life and he didn't have to. But even then, it hadn't hit me that we were probably just passing the friendship barrier into something more, like Maggie and April were telling me any chance they got. It wasn't until he came over one day a week after Aiden was born, telling me to sleep and that he would watch Aiden for a bit, that it hit me, this isn't just a normal friendship."

She seemed to be finished, so Will continued, "She woke up about 6 hours later and I was sitting on the couch, Aiden was asleep. I was getting up to leave when she stopped me and kissed me. I tried to brush it off saying it was only because she was sleep-deprived and she didn't know what she was doing, but she wouldn't let me." He chuckled and kissed Natalie's temple. "And the rest as you would say, Jay, is history. Because you are cheesy like that."

Erin sighed, "Jay, I hate to say it, but they are probably cuter than us."

Jay nodded, "Will, I think you've got yourself a keeper there."

"Don't I know it." Will leaned over to kiss the side of Natalie's head again, this time savoring it for just a bit longer. "So, I think it's safe to say that she's passed your test to see if she's good for me or not."

Erin looked at him incredulously, "Uh, no. The only test was to see if she was too good for you. And she kinda is, but I think you've roped this one in pretty good."

"Sadly." Jay said under his breath. Erin kicked him the shin. "Oww."

The waiter approached the table with only one check and before Jay could grab it and see how much he had to pay, Will snatched it from him, "I got it. Don't worry."

"Dude, we were the ones that invited you guys out to dinner."

"Exactly. Which is why I'm paying. It's the least I could do." Before Jay could argue back, Erin pinched his leg to make sure this little argument wouldn't become anything bigger.

The rest of the dinner was spent with more light-hearted conversation before they headed out.

* * *

As they approached Erin's condominium building, Natalie looked towards the backseat, "Thank you again for inviting me to dinner. It was kind of fun. We should do it again sometime." Erin and Jay smiled back at her.

"It was fun." It was silent for a moment and Natalie turned back around to face forward. "Oh and Natalie, if you ever want me and Jay to babysit Aiden, we would be happy to."

Natalie glance back at her, "Thank you. I might have to take you up on that sometime." She smiled.

"And we are here." Will said as he pulled up in front of the lobby door, "Don't have too much fun tonight kids."

Jay huffed back to him, "Could say the same to you."

"Thanks for driving Will and for paying for dinner. And Natalie, it was nice to get to know you a bit. I think we should have a girl's night sometime, get some girl time away from these bozos."

"Definitely. See you guys later."

Jay extended a hand to Erin to help her out of the car and then proceeded to shut the car door behind her. They walked hand-in-hand for the short walk into the building. Jay spoke first, "I like her. I mean I know I've met her before and all, but this was the first time she really opened up. One thing is for sure though, Will does not deserve her."

"But maybe he does. I mean you probably don't deserve me but he we are." She laughed.

"True." He laughed with her.

* * *

Thirty minutes later, Natalie and Will were snuggled up on the couch sort of watching a movie. "See this is what I really love doing with you. Just being kind of lazy, sitting on the couch and relaxing after a hectic day." Will said as his fingers lightly grazed her back under the t-shirt she was wearing. "And you wearing one of my t-shirts and sweatpants doesn't hurt." He felt her trying to muffle a laugh against his chest.

"As much as I hate to admit it, tonight was kind of fun. Erin isn't as intense as I thought she was. And she's kind of protective over you which is really sweet."

"Yeah, ever since her and Jay started dating, I've noticed that she's really protective of her family: the Intelligence Unit, Jay, so I guess I might fall under that family category too. And now you too I hope."

"I hope they make it. They seem really happy together."

"Me too. And since I know you can keep a secret, Jay asked me a few weeks ago for my mom's ring. She gave it to me to make sure Jay didn't just give it to anyone. I think he'll propose soon, I just hope it won't scare Erin away. From what I hear, commitment has been kinda hard for those two."

"But you also said they went public about a year ago, so that at least shows they somewhat have committed to their relationship for however long."

"Yeah." Will remained silent for a few seconds. "Hey, just so you know, I'm committed to this. For the long haul. I don't want that to scare you, but you are it for me. I never in my life thought I would say that or even think that, but Nat, I have never been able to be myself or feel comfortable in a relationship. And I know you can't really say the same about me because of Jeff and all, but…"

"Stop." Natalie lifted her head off his chest to look him in the eyes, "I can never compare the two of you. It's just not fair, but what I do know is that you make me happy and I haven't been truly happy in a really long time. My life feels whole now. I have a beautiful 6-month year old boy who is healthy and you, you make me feel safe and I love that." Will smiled down at her and placed a sweet kiss on her lips. "Well, we might as well make the best of our night with no interruptions." She smirked as she sat up in order to straddle his hips. Their kisses increasing with passion.

Will interrupted the mini make out session, "To the bedroom?"

"Mm hmm." She responded. He whisked her up in his arms, her legs around his waist and nipped at her neck as he walked them to his bedroom. "Will. Stop, you know that's my tickle spot." She giggled.

"Fine. as long as you promise we get to cuddle after this. I love your cuddles." He looked at her with a puppy dog face.

She laughed, "I promise."

"Good." He went back to kissing her senselessly as he laid her gently on the bed.

 **AN (cont.): Thanks for reading! Please review or pm me with your comments or future fic ideas. (I may just write them even if I don't have time lol.)**

 **Or follow me on tumblr if you want to get a hold of me or just follow me bc you love Linstead, Chicago Med, Quantico and many more! Link in bio or just search linsteadlover and I should pop up!**


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